The Scripps Research Institute Chemists uncover click chemistry reactivity

Researchers uncover click chemistry reactivity

11:11 AM, 18th August 2014
The Scripps Research Institute Chemists uncover click chemistry reactivity
K Barry Sharpless, Chemist, The Scripps Research Institute.

LA JOLLA, US: Chemists led by Nobel laureate K Barry Sharpless at The Scripps Research Institute (TSRI) have used his click chemistry to uncover unprecedented, powerful reactivity for making new drugs, diagnostics, plastics, smart materials and many other products.

The new SuFEx - Sulfur Fluoride Exchange - reactions enable chemists to link molecules of their choice together using derivatives of a common commercial chemical considered essentially inert. The Sharpless team made this chemical reliably and predictably reactive. Astonishingly, acid-base constraints are rarely a concern, though they are central to nature’s chemistry and an enormous hurdle for chemists. The stabile linkers are also non-polar and can enter cells, so have potential for crossing the blood-brain barrier. Consequently, SuFEx gives easy access to an entire, unexplored galaxy within the chemical universe.

Click chemistry, conceived in the mid-90s as a method for discovering new and improving existing chemical reactivity, became universally used in the chemical sciences after the 2002 discovery of copper-catalyzed azide-alkyne cycloaddition (CuAAC). Now SuFEx is the second “perfect” click reaction to be discovered at TSRI.

“This is a new, emergent phenomenon,” said Sharpless, the WM Keck Professor of Chemistry and member of the Skaggs Institute for Chemical Biology at TSRI.

“Sulfer fluoride compounds are known for their high stability, yet we eventually realized that there are ways to make them usefully reactive - the speed and varied reaction environment it tolerates is amazing,” said Jiajia Dong, Research Associate, TSRI.

One of the most exciting potential uses of SuFEx is the promise of finding new diagnostics, drugs and other therapeutics, even ones reactive within the human body. TSRI chemists are already using SuFEx reactivity for the precision assembly of new molecules from diverse building blocks. This should quickly lead to reduced manufacturing costs for equivalents of existing products, as well as the introduction of new products made by easy synthetic routes. “We believe that we can, with near-perfect control, use sulfur fluorides as general connectors for joining molecular building blocks,” said Dong.

The reaction easily creates polysulfate plastics, a whole class of unexplored of materials. Polysulfate plastics may, for example, have properties to rival or surpass those of popular, ubiquitous polymers like polycarbonates. Strong, resilient and transparent, polycarbonates are annually produced in the millions of tonne and are found everywhere in consumer products, from DVDs to the cockpit canopies of F-22 Raptor jets. Yet polycarbonates “hydrolize”- break down in water - rather easily. A consequence is the much-publicized leaching of bis-phenol-A, the principal building block of all polycarbonates and an estrogen mimic.

A stable, non-leaching commercial polysulfate is an obvious target for SuFEx. Chemists have long assumed polysulfates could not be made by a commercially feasible method, but in a strikingly easy, controlled and scalable process, the Sharpless team made BPA polysulfate fibers.

“Initial tests indicate this new plastic may be more resistant to impact and degradation than polycarbonates. But this was just one demonstration of the technique. The control and the selectivity that we have in this process mean that we can polymerize a wide variety of different building blocks,” said Dong.

© The Scripps Research Institute News

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